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1.
J Chem Ecol ; 49(1-2): 67-76, 2023 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-36484901

RESUMEN

The common grass yellow butterfly, Eurema mandarina is a Fabaceae-feeding species, the females of which readily oviposit on Albizia julibrissin and Lespedeza cuneata in mainland Japan. We previously demonstrated that the methanolic leaf extracts of these plants, and their highly polar aqueous fractions strongly elicit female oviposition. Furthermore, the three subfractions obtained by ion-exchange chromatographic separation of the aqueous fraction have been found to be less effective alone, but synergistically stimulate female oviposition when combined. This indicates that female butterflies respond to multiple compounds with different acidity. We have previously identified d-pinitol from the neutral/amphoteric subfractions and glycine betaine from the basic subfractions as oviposition stimulants of E. mandarina. The present study aimed to identify active compounds in the remaining acidic subfractions of A. julibrissin and L. cuneata leaf extracts. GC-MS analyses of trimethylsilyl-derivatized samples revealed the presence of six compounds in the acidic subfractions. In bioassays using these authentic chemicals, erythronic acid (EA) and threonic acid (TA) were moderately active in eliciting oviposition responses in E. mandarina, with their d-isomers showing slightly higher activity than their l-isomers. Female responsiveness differed between d-EA and l-TA, the major isomers of these compounds in plants, with the response to d-EA reaching a plateau at concentrations above 0.005% and that to l-TA peaking at a concentration of 0.01%. The natural concentrations of d-EA and l-TA in fresh A. julibrissin and L. cuneata leaves were sufficient to stimulate oviposition. Furthermore, mixing 0.001% d-EA or 0.001% l-TA, to which females are mostly unresponsive, with 0.1% d-pinitol resulted in a synergistic enhancement of the oviposition response. These findings demonstrate that E. mandarina females utilize both polyhydroxy acids, EA and TA, as chemical cues for oviposition.


Asunto(s)
Mariposas Diurnas , Animales , Femenino , Mariposas Diurnas/fisiología , Oviposición , Extractos Vegetales/química , Inositol/química , Plantas
2.
Molecules ; 27(18)2022 Sep 16.
Artículo en Inglés | MEDLINE | ID: mdl-36144793

RESUMEN

Eight new inositol derivatives, solsurinositols A-H (1-8), were isolated from the 70% EtOH extract of the leaves of Solanum capsicoides Allioni. Careful isolation by silica gel column chromatography followed by preparative high-performance liquid chromatography (HPLC) allowed us to obtain analytically pure compounds 1-8. They shared the same relative stereochemistry on the ring but have different acyl groups attached to various hydroxyl groups. This was the first time that inositol derivatives have been isolated from this plant. The chemical structures of compounds 1-8 were characterized by extensive 1D nuclear magnetic resonance (NMR) and 2D NMR and mass analyses. Meanwhile, the in vitro anti-inflammatory activity of all compounds was determined using lipopolysaccharide (LPS)-induced BV2 microglia, and among the isolates, compounds 5 (IC50 = 11.21 ± 0.14 µM) and 7 (IC50 = 14.5 ± 1.22 µM) were shown to have potential anti-inflammatory activity.


Asunto(s)
Solanum , Antiinflamatorios/química , Antiinflamatorios/farmacología , Inositol/química , Inositol/farmacología , Lipopolisacáridos/farmacología , Extractos Vegetales/farmacología , Hojas de la Planta , Gel de Sílice , Solanum/química
3.
Int J Mol Sci ; 22(19)2021 Sep 30.
Artículo en Inglés | MEDLINE | ID: mdl-34638926

RESUMEN

Myo-inositol (myo-Ins) and D-chiro-inositol (D-chiro-Ins) are natural compounds involved in many biological pathways. Since the discovery of their involvement in endocrine signal transduction, myo-Ins and D-chiro-Ins supplementation has contributed to clinical approaches in ameliorating many gynecological and endocrinological diseases. Currently both myo-Ins and D-chiro-Ins are well-tolerated, effective alternative candidates to the classical insulin sensitizers, and are useful treatments in preventing and treating metabolic and reproductive disorders such as polycystic ovary syndrome (PCOS), gestational diabetes mellitus (GDM), and male fertility disturbances, like sperm abnormalities. Moreover, besides metabolic activity, myo-Ins and D-chiro-Ins deeply influence steroidogenesis, regulating the pools of androgens and estrogens, likely in opposite ways. Given the complexity of inositol-related mechanisms of action, many of their beneficial effects are still under scrutiny. Therefore, continuing research aims to discover new emerging roles and mechanisms that can allow clinicians to tailor inositol therapy and to use it in other medical areas, hitherto unexplored. The present paper outlines the established evidence on inositols and updates on recent research, namely concerning D-chiro-Ins involvement into steroidogenesis. In particular, D-chiro-Ins mediates insulin-induced testosterone biosynthesis from ovarian thecal cells and directly affects synthesis of estrogens by modulating the expression of the aromatase enzyme. Ovaries, as well as other organs and tissues, are characterized by a specific ratio of myo-Ins to D-chiro-Ins, which ensures their healthy state and proper functionality. Altered inositol ratios may account for pathological conditions, causing an imbalance in sex hormones. Such situations usually occur in association with medical conditions, such as PCOS, or as a consequence of some pharmacological treatments. Based on the physiological role of inositols and the pathological implications of altered myo-Ins to D-chiro-Ins ratios, inositol therapy may be designed with two different aims: (1) restoring the inositol physiological ratio; (2) altering the ratio in a controlled way to achieve specific effects.


Asunto(s)
Diabetes Gestacional/tratamiento farmacológico , Inositol/farmacología , Síndrome del Ovario Poliquístico/tratamiento farmacológico , Testosterona/metabolismo , Células Tecales/efectos de los fármacos , Diabetes Gestacional/metabolismo , Femenino , Humanos , Inositol/química , Inositol/metabolismo , Estructura Molecular , Síndrome del Ovario Poliquístico/metabolismo , Embarazo , Transducción de Señal/efectos de los fármacos , Células Tecales/metabolismo
4.
Nutrients ; 13(7)2021 Jun 30.
Artículo en Inglés | MEDLINE | ID: mdl-34209137

RESUMEN

D-Pinitol (DPIN) is a natural occurring inositol capable of activating the insulin pathway in peripheral tissues, whereas this has not been thoroughly studied in the central nervous system. The present study assessed the potential regulatory effects of DPIN on the hypothalamic insulin signaling pathway. To this end we investigated the Phosphatidylinositol-3-kinase (PI3K)/Protein Kinase B (Akt) signaling cascade in a rat model following oral administration of DPIN. The PI3K/Akt-associated proteins were quantified by Western blot in terms of phosphorylation and total expression. Results indicate that the acute administration of DPIN induced time-dependent phosphorylation of PI3K/Akt and its related substrates within the hypothalamus, indicating an activation of the insulin signaling pathway. This profile is consistent with DPIN as an insulin sensitizer since we also found a decrease in the circulating concentration of this hormone. Overall, the present study shows the pharmacological action of DPIN in the hypothalamus through the PI3K/Akt pathway when giving in fasted animals. These findings suggest that DPIN might be a candidate to treat brain insulin-resistance associated disorders by activating insulin response beyond the insulin receptor.


Asunto(s)
Hipotálamo/metabolismo , Inositol/análogos & derivados , Fosfatidilinositol 3-Quinasa/metabolismo , Proteínas Proto-Oncogénicas c-akt/metabolismo , Transducción de Señal , Administración Oral , Animales , Glucemia/metabolismo , Activación Enzimática/efectos de los fármacos , Glucagón/sangre , Homeostasis , Hipotálamo/efectos de los fármacos , Inositol/administración & dosificación , Inositol/sangre , Inositol/química , Inositol/farmacología , Insulina/sangre , Insulina/metabolismo , Resistencia a la Insulina , Factor I del Crecimiento Similar a la Insulina/metabolismo , Masculino , Fosforilación/efectos de los fármacos , Ratas Wistar , Transducción de Señal/efectos de los fármacos
5.
Chem Biol Drug Des ; 98(4): 539-560, 2021 10.
Artículo en Inglés | MEDLINE | ID: mdl-34173346

RESUMEN

The alpha (α)-amylase is a calcium metalloenzyme that aids digestion by breaking down polysaccharide molecules into smaller ones such as glucose and maltose. In addition, the enzyme causes postprandial hyperglycaemia and blood glucose levels to rise. α-Amylase is a well-known therapeutic target for the treatment and maintenance of postprandial blood glucose elevations. Various enzymatic inhibitors, such as acarbose, miglitol and voglibose, have been found to be effective in targeting this enzyme, prompting researchers to express an interest in developing potent alpha-amylase inhibitor molecules. The review mainly focused on designing different derivatives of drug molecules such as benzofuran hydrazone, indole hydrazone, spiroindolone, benzotriazoles, 1,3-diaryl-3-(arylamino) propan-1-one, oxadiazole and flavonoids along with their target-receptor interactions, IC50 values and other biological activities.


Asunto(s)
Diabetes Mellitus/tratamiento farmacológico , Inhibidores de Glicósido Hidrolasas/química , Hipoglucemiantes/química , alfa-Amilasas/metabolismo , 1-Desoxinojirimicina/análogos & derivados , 1-Desoxinojirimicina/química , Acarbosa/química , Benzofuranos/química , Glucemia/efectos de los fármacos , Descubrimiento de Drogas , Flavonoides/química , Inhibidores de Glicósido Hidrolasas/farmacología , Humanos , Hidrazonas/química , Hipoglucemiantes/farmacología , Indoles/química , Inositol/análogos & derivados , Inositol/química , Oxadiazoles/química , Relación Estructura-Actividad
6.
Methods Mol Biol ; 2295: 365-378, 2021.
Artículo en Inglés | MEDLINE | ID: mdl-34047987

RESUMEN

The phosphate esters of myo-inositol (Ins) occur ubiquitously in biology. These molecules exist as soluble or membrane-resident derivatives and regulate a plethora of cellular functions including phosphate homeostasis, DNA repair, vesicle trafficking, metabolism, cell polarity, tip-directed growth, and membrane morphogenesis. Phosphorylation of all inositol hydroxyl groups generates phytic acid (InsP6), the most abundant inositol phosphate present in eukaryotic cells. However, phytic acid is not the most highly phosphorylated naturally occurring inositol phosphate. Specialized small molecule kinases catalyze the formation of the so-called myo-inositol pyrophosphates (PP-InsPs), such as InsP7 and InsP8. These molecules are characterized by one or several "high-energy" diphosphate moieties and are ubiquitous in eukaryotic cells. In plants, PP-InsPs play critical roles in immune responses and nutrient sensing. The detection of inositol derivatives in plants is challenging. This is particularly the case for inositol pyrophosphates because diphospho bonds are labile in plant cell extracts due to high amounts of acid phosphatase activity. We present two steady-state inositol labeling-based techniques coupled with strong anion exchange (SAX)-HPLC analyses that allow robust detection and quantification of soluble and membrane-resident inositol polyphosphates in plant extracts. These techniques will be instrumental to uncover the cellular and physiological processes controlled by these intriguing regulatory molecules in plants.


Asunto(s)
Cromatografía Líquida de Alta Presión/métodos , Fosfatos de Inositol/química , Resinas de Intercambio Aniónico/química , Aniones/química , Arabidopsis/metabolismo , Proteínas de Arabidopsis/aislamiento & purificación , Proteínas de Arabidopsis/metabolismo , Inositol/química , Fosfatos de Inositol/metabolismo , Fosfatidilinositoles/química , Fosforilación , Plantas/química , Plantas/metabolismo , Polifosfatos/química , Semillas/química , Transducción de Señal/fisiología
7.
Eur Rev Med Pharmacol Sci ; 25(5): 2390-2402, 2021 03.
Artículo en Inglés | MEDLINE | ID: mdl-33755975

RESUMEN

OBJECTIVE: Inositol is a carbocyclic sugar polyalcohol. By epimerization of its hydroxyl groups, nine possible stereoisomers can be generated, two of major physiological and clinical relevance: myo-inositol and D-chiro-inositol. Myo-inositol and D-chiro-inositol are normally stored in kidney, brain and liver and are necessary for functions, such as signal transduction, metabolic flux, insulin signaling, regulation of ion-channel permeability, stress response and embryo development. In this narrative review, we summarize the mechanisms by which myo-inositol and D-chiro-inositol can be synthesized and absorbed and their possible role in the etiopathogenesis of neural tube defects. MATERIALS AND METHODS: We performed an online search in the PubMed database using the following keywords: "inositol", "D-chiro-inositol", "myo-inositol", "neural tube defects and inositol". RESULTS: Inositol requirements are partly met by dietary intake, while the rest is synthesized endogenously. Inositol deficiency may be involved in the pathogenesis of diseases, such as metabolic syndrome, spina bifida (a neural tube defect), polycystic ovary syndrome and diabetes. Supplementation of the two inositol stereoisomers, D-chiro-inositol and myo-inositol is important to prevent these conditions. CONCLUSIONS: Inositol is fundamental for signal transduction in the brain, kidneys, reproductive organs and other tissues in response to neurotransmitters, hormones and growth factors. Various genes are involved in inositol metabolism and associated pathways. Altered inositol concentrations are observed in several diseases. Analysis of the genes involved in inositol metabolism may provide important information for the clinical management of these conditions.


Asunto(s)
Inositol/metabolismo , Animales , Humanos , Inositol/química , Inositol/genética , Conformación Molecular
8.
Genes (Basel) ; 11(7)2020 07 14.
Artículo en Inglés | MEDLINE | ID: mdl-32674373

RESUMEN

There is a need to enhance the production of bioactive secondary metabolites and to establish new production systems, e.g., for liver-protective compounds of Silybum marianum seeds. Quantifying and identifying the produced phytochemicals, and examining their protective effects against genotoxic agents, is of great interest. This study established a protocol for the qualitative and quantitative production of hepatoprotective compounds in cotyledon-derived Silybum marianum callus through optimized supplementation of the MS medium with the growth regulators 2,4-D, benzylaminopurine, myoinositol, and asparagine. High-performance liquid chromatography (HPLC) coupled with electrospray ionisation mass spectrometry (ESI-MS) allowed for identification and quantification of the produced compounds. None of the growth medium combinations supported a detectable production of silymarin. Instead, the generated calli accumulated phenolic acids, in particular chlorogenic acid and dicaffeoylquinic acid, as revealed by HPLC and mass spectrometric analysis. 4-Nitro-o-phenylenediamine (NPD) was employed in the AMES-test with Salmonella typhimurium strain TA98 because it is a potent mutagen for this strain. Results revealed that callus extract had a high anti-genotoxic activity with respect to standard silymarin but more evident with respect seed extract. The callus produced chlorogenic acid and dicaffeoylquinic acid, which revealed higher bioactivity than silymarin. Both compounds were not formed or could not be detected in the seeds of Silybum marianum Egyptian ecotype.


Asunto(s)
Antioxidantes/química , Flavonoides/química , Silybum marianum/genética , Silimarina/química , Asparagina/química , Compuestos de Bencilo/química , Cromatografía Líquida de Alta Presión , Cotiledón/genética , Egipto , Flavonoides/clasificación , Inositol/química , Silybum marianum/química , Fitoquímicos/química , Purinas/química , Semillas/química , Espectrometría de Masa por Ionización de Electrospray
9.
Poult Sci ; 99(2): 893-905, 2020 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-32036985

RESUMEN

Myo-inositol (MI) has gained relevance in physiology research during the last decade. As a constituent of animal cells, MI was proven to be crucial in several metabolic and regulatory processes. Myo-inositol is involved in lipid signaling, osmolarity, glucose, and insulin metabolism. In humans and rodents, dietary MI was assessed to be important for health so that MI supplementation appeared to be a valuable alternative for treatment of several diseases as well as for improvements in metabolic performance. In poultry, there is a lack of evidence not only related to specific species-linked metabolic processes but also about the effects of dietary MI on performance and health. This review intends to provide information about the meaning of dietary MI in animal metabolism as well as to discuss potential implications of dietary MI in poultry health and performance with the aim to identify open questions in poultry research.


Asunto(s)
Inositol/metabolismo , Aves de Corral/metabolismo , Alimentación Animal/análisis , Fenómenos Fisiológicos Nutricionales de los Animales , Animales , Dieta/veterinaria , Inositol/química
10.
Biomolecules ; 10(2)2020 01 21.
Artículo en Inglés | MEDLINE | ID: mdl-31973207

RESUMEN

A relatively high concentration of phytate in buckwheat malt, and the low activity of endogenous buckwheat phytases, both of which limit the effective use of substrates (starch, proteins, minerals) for fermentation and yeast metabolism, gives rise to the potential for application of phytases in beer production. This study aims at obtaining a 100% buckwheat wort with high bioactive cyclitols (myo-inositol and D-chiro-inositol) concentrations released by exogenous phytases and acid phosphatases. Two mashing programs were used in the study, i.e., (1) typical for basic raw materials, namely the well-established Congress method, and (2) optimized for phytase activity. The results indicated a nearly 50% increase in the level of bioactive myo-inositol and an 80% degradation of phytate in the wort as a result of simultaneous application of phytase and phosphatase enzymes in the mashing of buckwheat malt. In addition, high D-chiro-inositol concentrations were released from malt to the buckwheat wort. The concerted action of the two phytases significantly increased (19-44%) Zn2+ concentrations in wort. This may be of great importance during mash fermentation by Saccharomyces cerevisiae yeasts. There is a potential to develop technology for buckwheat beer production, which, in addition to being free from gluten, comprises high levels of bioactive myo- and D-chiro-inositols.


Asunto(s)
6-Fitasa/química , Cerveza , Fagopyrum/metabolismo , Fosfatos de Inositol/química , Inositol/química , Ácido Fítico/química , Cromatografía por Intercambio Iónico , Ciclitoles/química , Fermentación , Análisis de los Alimentos/métodos , Tecnología de Alimentos/métodos , Hidrólisis , Fosfatos de Inositol/metabolismo , Metales , Saccharomyces cerevisiae/metabolismo , Espectrofotometría Ultravioleta , Estereoisomerismo , Zinc
11.
J Chem Ecol ; 45(11-12): 926-933, 2019 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-31758292

RESUMEN

Chemical examination of plant constituents responsible for oviposition by a Magnoliaceae-feeding butterfly, Graphium doson, was conducted using its major host plant, Michelia compressa. A methanol extract prepared from young leaves of the plant elicited a strong oviposition response from females. The methanolic extract was then separated by solvent partition into three fractions: CHCl3, i-BuOH, and aqueous fractions. Active substance(s) resided in both i-BuOH- and water-soluble fractions. Bioassay-guided further fractionation of the water-soluble substances by means of various chromatographic techniques led to the isolation of an oviposition stimulant. The stimulant was identified as D-(+)-pinitol on the basis of 13C NMR spectra and physicochemical properties. D-(+)-Pinitol singly exhibited a moderate oviposition-stimulatory activity at a dose of 150 µg/cm2. This compound was present also in another host plant, Magnolia grandiflora, in a sufficient amount to induce oviposition behavior of G. doson females. Certain cyclitols including D-(+)-pinitol have been reported to be involved in stimulation of oviposition by some Aristolochiaceae- and Rutaceae-feeding papilionid butterflies. A possible pathway of phytochemical-mediated host shifts in the Papilionidae, in which certain cyclitols could enact important mediators, is discussed in relation to the evolution of cyclitol biosynthesis in plants.


Asunto(s)
Magnolia/química , Oviposición/efectos de los fármacos , Extractos Vegetales/química , Animales , Butanoles/química , Mariposas Diurnas , Ciclitoles/química , Ciclitoles/metabolismo , Femenino , Especificidad del Huésped , Interacciones Huésped-Parásitos , Inositol/análogos & derivados , Inositol/química , Inositol/metabolismo , Magnolia/metabolismo , Extractos Vegetales/metabolismo , Hojas de la Planta/química , Hojas de la Planta/metabolismo , Solubilidad , Agua/química
12.
Parkinsonism Relat Disord ; 62: 185-191, 2019 05.
Artículo en Inglés | MEDLINE | ID: mdl-30558837

RESUMEN

INTRODUCTION: Several structural and functional neuroimaging studies have shown that the Supplementary Motor Area (SMA) is affected by tau pathology in patients with Progressive Supranuclear Palsy (PSP). The aim of the study was to investigate the biochemical profile of SMA in PSP patients, using proton magnetic resonance spectroscopy (1H-MRS). METHODS: Sixteen PSP patients and 18 healthy controls participated in this study. 1H-MRS was performed by using a Point RESolving Spectroscopy (PRESS) single-voxel sequence implemented on a 3-T scanner. A voxel of 25 × 25 × 15 mm involving the right and left SMA was acquired in all subjects. Peak areas of N-acetyl-aspartate + N-acetyl-aspartyl-glutamate (NAA), creatine with phosphocreatine (Cr), glycerophosphocholine + phosphocholine (Cho), glutamate + glutamine (Glx), glutathione (GSH), myo-Inositol (mI) and Scyllo-Inositol (Scyllo) were calculated using a version 6.3-1K of the fitting program LCModel. Comparative analysis was performed on both absolute concentrations and ratio values relative to Cr. RESULTS: PSP patients showed a significant decrease in Scyllo concentration and Scyllo/Cr ratio values in SMA, compared to controls, whereas no difference between groups was found for the other ratio values. Of note, the attention and working memory functions were positively related to Scyllo and Scyllo/Cr values in PSP patients. CONCLUSIONS: Our study demonstrates that Scyllo and Scyllo/Cr were significantly reduced in the SMA of PSP patients. Because Scyllo seems to be able to protect against formation of toxic fibrils of amyloid-beta fragments and tau oligomers deposition, these preliminary findings may open new perspectives to investigate Scyllo as a new potential disease-modifying therapy for PSP.


Asunto(s)
Inositol/metabolismo , Corteza Motora/metabolismo , Espectroscopía de Protones por Resonancia Magnética/métodos , Parálisis Supranuclear Progresiva/diagnóstico , Parálisis Supranuclear Progresiva/metabolismo , Anciano , Biomarcadores/química , Biomarcadores/metabolismo , Femenino , Humanos , Inositol/química , Masculino , Persona de Mediana Edad , Estereoisomerismo
13.
Acta Diabetol ; 55(8): 805-812, 2018 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-29774465

RESUMEN

AIMS: Gestational diabetes mellitus (GDM) is the most common metabolic disorder of pregnancy. The aim of the study is to compare the effect of different dosages of inositol stereoisomers supplementation on insulin resistance levels and several maternal-fetal outcomes in GDM women. METHODS: Participants were randomly allocated to receive daily: 400 mcg folic acid (control treatment), 4000 mg myo-inositol plus 400 mcg folic acid (MI treatment), 500 mg D-chiro-inositol plus 400 mcg folic acid (DCI treatment) or 1100/27.6 mg myo/D-chiro-inositol plus 400 mcg folic acid (MI plus DCI treatment). The homeostasis model assessment of insulin resistance (HOMA-IR) was measured at the diagnosis of GDM and after 8 weeks of treatment. Secondary outcomes, obstetric outcomes and any maternal or fetal complication at delivery were also collected. RESULTS: Eighty GDM women were assigned to one of the four arms of study (20 per arm). A significant delta decrease in HOMA-IR index was found in subjects of MI group without insulin therapy compared to control group (p < 0.001). A lower variation in average weight gain (at delivery vs pre-pregnancy and OGTT period) was detected in MI group vs control group (p = 0.001 and p = 0.019, respectively). Moreover, women exposed to MI and MI plus DCI required a significantly lower necessity of an intensified insulin treatment. Women of the control group had newborns with higher birth weight compared with women treated with inositol (p = 0.032). CONCLUSIONS: Our study provides interesting but preliminary results about the potential role of inositol stereoisomers supplementation in the treatment of GDM on insulin resistance levels and several maternal-fetal outcomes. Further studies are required to examine the optimal and effective dosages of different inositol supplements. CLINICAL TRIAL REG. NO.: NCT02097069, ClinicalTrial.gov.


Asunto(s)
Diabetes Gestacional/tratamiento farmacológico , Inositol/administración & dosificación , Adolescente , Adulto , Diabetes Gestacional/metabolismo , Relación Dosis-Respuesta a Droga , Femenino , Humanos , Inositol/química , Resistencia a la Insulina , Persona de Mediana Edad , Embarazo , Resultado del Embarazo , Estereoisomerismo , Adulto Joven
14.
Nat Prod Res ; 32(12): 1481-1483, 2018 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-28714347

RESUMEN

Four Melodinus species with antifungal activity were found in survey of the floral resources, in Shiwan Mountain Natural Reserve, Guangxi Province, China. Crude methanolic extracts of the twigs and leaves of Melodinus suaveolens exhibited potent antifungal activities against the plant pathogenic fungi Colletotrichum musae, Colletotrichum graminicola, Colletotrichum gloeosporioides and Alternaria musae, and the ethyl acetate fraction inhibited these pathogens at rates of 85.37, 91.47, 72.77 and 89.87%, respectively (5 mg/mL). A new compound, (2R, 3S, 5S, 6R)-1-O-methyl- chiro-inositol was isolated from the ethyl acetate fraction, along with 15 known compounds. The antifungal activities of compounds (1-16) were evaluated for the first time. Compound (4) had potent antifungal activity against C. gloeosporioides, C. graminicola and A. musae.


Asunto(s)
Apocynaceae/química , Fungicidas Industriales/farmacología , Inositol/análogos & derivados , Inositol/farmacología , Extractos Vegetales/química , Alternaria/efectos de los fármacos , China , Colletotrichum/efectos de los fármacos , Evaluación Preclínica de Medicamentos , Fungicidas Industriales/química , Inositol/química , Metanol/química , Enfermedades de las Plantas/microbiología , Extractos Vegetales/farmacología , Hojas de la Planta/química
15.
Molecules ; 22(8)2017 Aug 14.
Artículo en Inglés | MEDLINE | ID: mdl-28805750

RESUMEN

In this study, the characterization of chemical constituents and biological activity of the roots of Taraxacum coreanum (Asteraceae) was attempted. Phytochemical investigation of the roots of T. coreanum led to the isolation of two new inositol derivatives, taraxinositols A (1) and B (2), and a new phenolic compound, taraxinol (16), together with twenty known compounds including four inositol derivatives, neo-inositol-1,4-bis (4-hydroxybenzeneacetate) (3), chiro-inositol-1,5-bis(4- hydroxybenzeneacetate) (4), chiro-inositol-2,3-bis (4-hydroxybenzeneacetate) (5) and chiro-inositol- 1,2,3-tris (4-hydroxybenzeneacetate) (6), nine phenolic compounds: p-hydroxybenzaldehyde (7), vanillin (8), syringaldehyde (9), vanillic acid (10), 4-methoxyphenylacetic acid (11), 4-hydroxy- phenylacetic acid methyl ester (12), optivanin (13), isoferulic acid (14) and dihydroconiferyl alcohol (15), four coumarins: nodakenetin (17), decursinol (18), prangol (19) and isobyakangelicin (20), and three lignans: syringaresinol-4'-O-ß-d-glucoside (21), syringaresinol (22), and pinoresinol (23). The structures of isolated compounds were determined on the basis of spectroscopic analysis. Among the isolated compounds, vanillic acid, isoferulic acid and syringaresinol showed radical scavenging activity with IC50 values ranging from 30.4 to 75.2 µM.


Asunto(s)
Inositol/química , Fenol/química , Extractos Vegetales/química , Raíces de Plantas/química , Taraxacum/química , Antioxidantes/química , Antioxidantes/farmacología , Cromatografía Líquida de Alta Presión/métodos , Cumarinas/química , Furanos/química , Glucósidos/química , Humanos , Concentración 50 Inhibidora , Inositol/aislamiento & purificación , Lignanos/química , Espectroscopía de Resonancia Magnética/métodos , Fenol/aislamiento & purificación , Extractos Vegetales/aislamiento & purificación , Receptores Depuradores/química , Receptores Depuradores/metabolismo
16.
Appl Environ Microbiol ; 83(16)2017 08 15.
Artículo en Inglés | MEDLINE | ID: mdl-28600316

RESUMEN

We developed an in vitro enzyme system to produce myo-inositol from starch. Four enzymes were used, maltodextrin phosphorylase (MalP), phosphoglucomutase (PGM), myo-inositol-3-phosphate synthase (MIPS), and inositol monophosphatase (IMPase). The enzymes were thermostable: MalP and PGM from the hyperthermophilic archaeon Thermococcus kodakarensis, MIPS from the hyperthermophilic archaeon Archaeoglobus fulgidus, and IMPase from the hyperthermophilic bacterium Thermotoga maritima The enzymes were individually produced in Escherichia coli and partially purified by subjecting cell extracts to heat treatment and removing denatured proteins. The four enzyme samples were incubated at 90°C with amylose, phosphate, and NAD+, resulting in the production of myo-inositol with a yield of over 90% at 2 h. The effects of varying the concentrations of reaction components were examined. When the system volume was increased and NAD+ was added every 2 h, we observed the production of 2.9 g myo-inositol from 2.9 g amylose after 7 h, achieving gram-scale production with a molar conversion of approximately 96%. We further integrated the pullulanase from T. maritima into the system and observed myo-inositol production from soluble starch and raw potato with yields of 73% and 57 to 61%, respectively.IMPORTANCEmyo-Inositol is an important nutrient for human health and provides a wide variety of benefits as a dietary supplement. This study demonstrates an alternative method to produce myo-inositol from starch with an in vitro enzyme system using thermostable maltodextrin phosphorylase (MalP), phosphoglucomutase (PGM), myo-inositol-3-phosphate synthase, and myo-inositol monophosphatase. By utilizing MalP and PGM to generate glucose 6-phosphate, we can avoid the addition of phosphate donors such as ATP, the use of which would not be practical for scaled-up production of myo-inositol. myo-Inositol was produced from amylose on the gram scale with yields exceeding 90%. Conversion rates were also high, producing over 2 g of myo-inositol within 4 h in a 200-ml reaction mixture. By adding a thermostable pullulanase, we produced myo-inositol from raw potato with yields of 57 to 61% (wt/wt). The system developed here should provide an attractive alternative to conventional methods that rely on extraction or microbial production of myo-inositol.


Asunto(s)
Proteínas Arqueales/química , Archaeoglobus fulgidus/enzimología , Inositol/química , Liasas Intramoleculares/química , Monoéster Fosfórico Hidrolasas/química , Almidón/química , Thermococcus/enzimología , Proteínas Arqueales/genética , Proteínas Arqueales/metabolismo , Estabilidad de Enzimas , Inositol/metabolismo , Liasas Intramoleculares/genética , Liasas Intramoleculares/metabolismo , NAD/metabolismo , Monoéster Fosfórico Hidrolasas/genética , Monoéster Fosfórico Hidrolasas/metabolismo , Almidón/metabolismo
17.
Nat Prod Commun ; 11(3): 405-6, 2016 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-27169192

RESUMEN

The genus Retama (Fabaceae) is widely distributed in the Mediterranean region. In the present study, pinitol (3-O-methyl-chiro-inositol), an anti-inflammatory and antidiabetic molecule, was isolated from aerial parts of R. monosperma, and its structure established on the basis of spectroscopic techniques (1D/2D NMR) and MS. Identification and quantification of pinitol in R. raetam and R. sphaerocarpa were also performed. R. monosperma had the highest concentration of pinitol (2.3%). The presence of pinitol in aqueous extracts of Retama spp. may explain the adaptation of these plants to drought and salinity. Furthermore, pinitol could be considered as a mediator in the anti-inflammatory and hypoglycemic activities of Retama spp., which are traditionally used to treat diabetes.


Asunto(s)
Fabaceae/química , Inositol/análogos & derivados , Inositol/química , Estructura Molecular
18.
Curr Top Med Chem ; 16(6): 634-54, 2016.
Artículo en Inglés | MEDLINE | ID: mdl-26286213

RESUMEN

Ocular biology is a prominent area of research and advancement, as eyes are the most precious for us to see this beautiful world. Though we have overcome many ocular problems, but still challenges, no doubt exist in the path of the journey. Many ocular disorders still either have surgery or symptomatic drugs as a treatment. If we could get a better preventive way or single drug with many and more potential effects, will definitely be a boon for our society. Keeping the way we tried to focus on the impending effects of phytochemicals on some important ocular disorders. Our study promised with virtual screening based on important insilico protocols that can be a landmark for better futuristic approach towards novel drug development. As a selection Eales' Disease, Diabetic Retinopathy, Uveitis, Age related Macular Disorder, CRVO were taken. Causative Protein identification is the basic of study and further advance Insilico approaches were based on this target in respective disorders. Retinol Binding protein-3 and Retinal S antigen protein in case of Eales, Erythropoietin in the case of Diabetic Retinopathy, Nucleotide-binding oligomerization domain-containing protein-2 in case of Uveitis, Hemicentin-1 in case of Age related Macular Disorder, Coagulation Factor-V in case of CRVO were identified. Insilico characterization, Secondary and Tertiary structure prediction makes the study more prominent towards virtual screening. Virtual Screening was based on the parameters of docking, which reflects the potentiality of Ginkgolide, D-pinitol, Gugglesterones, Berberine and Curcumin herbal molecules against above mentioned ocular disorders respectively. Study signifies about the spectacular vision of herbal uses just to limit the vast side effects of synthetic chemicals used as ocular drugs.


Asunto(s)
Berberina/uso terapéutico , Curcumina/uso terapéutico , Oftalmopatías/tratamiento farmacológico , Ginkgólidos/uso terapéutico , Medicina de Hierbas , Inositol/análogos & derivados , Berberina/química , Biología Computacional , Curcumina/química , Evaluación Preclínica de Medicamentos , Ginkgólidos/química , Humanos , Inositol/química , Inositol/uso terapéutico , Modelos Moleculares , Plantas Medicinales/química
19.
Cochrane Database Syst Rev ; (12): CD011507, 2015 Dec 17.
Artículo en Inglés | MEDLINE | ID: mdl-26678256

RESUMEN

BACKGROUND: Gestational diabetes, glucose intolerance with onset or first recognition during pregnancy, is a rising problem worldwide. Both non-pharmacological and pharmacological approaches to the prevention of gestational diabetes have been, and continue to be explored. Myo-inositol, an isomer of inositol, is a naturally occurring sugar commonly found in cereals, corn, legumes and meat. It is one of the intracellular mediators of the insulin signal and correlated with insulin sensitivity in type 2 diabetes. The potential beneficial effect on improving insulin sensitivity suggests that myo-inositol may be useful for women in preventing gestational diabetes. OBJECTIVES: To assess if antenatal dietary supplementation with myo-inositol is safe and effective, for the mother and fetus, in preventing gestational diabetes. SEARCH METHODS: We searched the Pregnancy and Childbirth Group's Trials Register, ClinicalTrials.gov, WHO ICTRP (2 November 2015) and reference lists of retrieved studies. SELECTION CRITERIA: We sought published and unpublished randomised controlled trials, including conference abstracts, assessing the effects of myo-inositol for the prevention of gestational diabetes mellitus (GDM). Quasi-randomised and cross-over trials were not eligible for inclusion, but cluster designs were eligible. Participants in the trials were pregnant women. Women with pre-existing type 1 or type 2 diabetes were excluded. Trials that compared the administration of any dose of myo-inositol, alone or in a combination preparation were eligible for inclusion. Trials that used no treatment, placebo or another intervention as the comparator were eligible for inclusion. DATA COLLECTION AND ANALYSIS: Two review authors independently assessed trials for inclusion, risk of bias and extracted the data. Data were checked for accuracy. MAIN RESULTS: We included four randomised controlled trials (all conducted in Italy) reporting on 567 women who were less than 11 weeks' to 24 weeks' pregnant at the start of the trials. The trials had small sample sizes and one trial only reported an interim analysis. Two trials were open-label. The overall risk of bias was unclear.For the mother, supplementation with myo-inositol was associated with a reduction in the incidence of gestational diabetes compared with control (risk ratio (RR) 0.43, 95% confidence interval (CI) 0.29 to 0.64; three trials; n = 502 women). Using GRADE methods this evidence was assessed as low with downgrading due to unclear risk of bias for allocation concealment in two of the included trials and lack of generalisability of findings. For women who received myo-inositol supplementation, the incidence of GDM ranged from 8% to 18%; for women in the control group, the incidence of GDM was 28%, using International Association of Diabetes and Pregnancy Study Groups Consensus Panel 2010 criteria to diagnose GDM.Two trials reported on hypertensive disorders of pregnancy, a primary maternal outcome of this review. There was no clear difference in risk of hypertensive disorders of pregnancy between the myo-inositol and control groups (average RR 0.43, 95% CI 0.02 to 8.41; two trials; n = 398 women; Tau(2) = 3.23; I(2) = 69%). Using GRADE methods, this evidence was assessed as very low, with downgrading due to wide confidence intervals with very low event rates, a small sample size, and lack of blinding and unclear allocation concealment methods, and a lack of generalisability. For women who received myo-inositol the risk of hypertensive disorders of pregnancy ranged from 0% to 33%; for women in the control group the risk was 4%.For the infant, none of the included trials reported on the primary neonatal outcomes of this systematic review (large-for-gestational age, perinatal mortality, mortality or morbidity composite).In terms of this review's secondary outcomes, there was no clear difference in the risk of caesarean section between the myo-inositol and control groups (RR 0.95, 95% CI 0.76 to 1.19; two trials; n = 398 women). Using GRADE methods, this evidence was assessed as low, with downgrading due to unclear risk of bias in one trial and lack of generalisability. For women who received myo-inositol supplementation, the risk of having a caesarean section ranged from 34% to 54%; for women in the control group the was 45%. There were no maternal adverse effects of therapy in the two trials that reported on this outcome (the other two trials did not report this outcome).Two trials found no clear difference in the risk of macrosomia between infants whose mothers received myo-inositol supplementation compared with controls (average RR 0.35, 95% CI 0.02 to 6.37; two trials; n = 398 infants;Tau(2) = 3.33; I(2) = 73%). Similarly, there was no clear difference between groups in terms of neonatal hypoglycaemia (RR 0.36, 95% CI 0.01 to 8.66) or shoulder dystocia (average RR 2.33, 95% CI 0.12 to 44.30, Tau(2) = 3.24; I(2) = 72%).There was a lack of data available for a large number of maternal and neonatal secondary outcomes, and no data for any of the long-term childhood or adulthood outcomes, or for health service cost outcomes. AUTHORS' CONCLUSIONS: Evidence from four trials of antenatal dietary supplementation with myo-inositol during pregnancy shows a potential benefit for reducing the incidence of gestational diabetes. No data were reported for any of this review's primary neonatal outcomes. There were very little outcome data for the majority of this review's secondary outcomes. There is no clear evidence of a difference for macrosomia when compared with control.The current evidence is based on small trials that are not powered to detect differences in outcomes including perinatal mortality and serious infant morbidity. All of the included studies were conducted in Italy which raises concerns about the lack of generalisability of the evidence to other settings. There is evidence of inconsistency and indirectness and as a result, many of the judgements on the quality of the evidence were downgraded to low or very low quality (GRADEpro Guideline Development Tool).Further trials for this promising antenatal intervention for preventing gestational diabetes are encouraged and should include pregnant women of different ethnicities and varying risk factors and use of myo-inositol (different doses, frequency and timing of administration) in comparison with placebo, diet and exercise or pharmacological interventions. Outcomes should include potential harms including adverse effects.


Asunto(s)
Diabetes Gestacional/prevención & control , Inositol/uso terapéutico , Atención Prenatal , Diabetes Gestacional/epidemiología , Femenino , Humanos , Incidencia , Inositol/efectos adversos , Inositol/química , Isomerismo , Embarazo , Ensayos Clínicos Controlados Aleatorios como Asunto
20.
J Nat Prod ; 78(10): 2332-8, 2015 Oct 23.
Artículo en Inglés | MEDLINE | ID: mdl-26444098

RESUMEN

Twelve new inositol derivatives, classified into myoinositol (1-6) and l-inositol (10-15) types, along with five known analogues were isolated from the whole plant of Inula cappa. The structures of the new compounds were established by extensive analysis of mass spectrometric and 1D and 2D NMR spectroscopic data. All the tested compounds showed anti-inflammatory activities against the production of NO in RAW264.7 macrophages stimulated by lipopolysaccharide, with IC50 values ranging from 7 to 23 µM.


Asunto(s)
Antiinflamatorios no Esteroideos , Medicamentos Herbarios Chinos , Inositol , Inula/química , Animales , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/aislamiento & purificación , Antiinflamatorios no Esteroideos/farmacología , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Concentración 50 Inhibidora , Inositol/análogos & derivados , Inositol/química , Inositol/aislamiento & purificación , Inositol/farmacología , Lipopolisacáridos/farmacología , Macrófagos/efectos de los fármacos , Ratones , Estructura Molecular , Óxido Nítrico/biosíntesis , Resonancia Magnética Nuclear Biomolecular , Componentes Aéreos de las Plantas/química
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